Mannich base

A Mannich base is a beta-amino-ketone, which is formed in the reaction of an amine, formaldehyde (or an aldehyde) and a carbon acid.[1] The Mannich base is an endproduct in the Mannich reaction, which is nucleophilic addition reaction of a non-enolizable aldehyde and any primary or secondary amine to produce resonance stabilized imine (iminium ion or imine salt). The addition of a carbanion from a CH acidic compound (any enolizable carbonyl compound, amide, carbamate, hydantoin or urea) to the imine gives the Mannich base.[2]

Base catalysed Mannich reaction forming Mannich base

  1. ^ March, Jerry (1985), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 3rd edition, New York: Wiley, ISBN 9780471854722, OCLC 642506595
  2. ^ Mannich base applied in this example: V. J. Belinelo; G. T. Reis; G. M. Stefani; D. L. Ferreira-Alves; D. Piló-Veloso (2002). "Synthesis of 6a,7b-dihydroxyvouacapan-17b-oic acid derivatives. Part IV: mannich base derivatives and its activities on the electrically stimulated Guinea-pig ileum preparation" (open access). Journal of the Brazilian Chemical Society. 13 (6): 830–837. doi:10.1590/S0103-50532002000600016.